Pentenone → 2,4-Dimethyl-5,6-dimethoxy-8-nitroquinoline

HRID 1863115

Reaction equation

HRID 1863115 reaction equation
[CH3:1][O:2][C:3]1[C:9]([O:10][CH3:11])=[CH:8][C:6]([NH2:7])=[C:5]([N+:12]([O-:14])=[O:13])[CH:4]=1.[CH3:15][C:16](=O)[CH:17]=[CH:18][CH3:19]>C1C=CC=CC=1.C(OCC)(=O)C>[CH3:11][O:10][C:9]1[C:3]([O:2][CH3:1])=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]2[C:8]=1[C:16]([CH3:15])=[CH:17][C:18]([CH3:19])=[N:7]2

Participants

4

Reactant 2

HCID 12248PentenoneHCID 46531524,5-Dimethoxy-2-nitroaniline

Product 1

HCID 6216122,4-Dimethyl-5,6-dimethoxy-8-nitroquinolineYield 14%

Reagents, catalysts & solvents 1

HCID 21583983Benzene ethyl acetateSolvent

Procedure

4,5-Dimethoxy-2-nitroaniline and 3-penten-2-one were subjected to a Skraup reaction. A black, tarry substance was obtained, from which an orange solid could be isolated by chromatography over silica gel using benzene-ethyl acetate (19:1) to elute the product. That material was thrice crystallized from 2-propanol, re-chromatographed, and again crystallized to afford 14% yield of golden 5,6-dimethoxy-2,4-dimethyl-8-nitroquinoline. Although it melted 85°-108°, it showed a single spot on two tlc systems.

Workup

  1. customA black, tarry substance was obtained, from which an orange solid
  2. customcould be isolated by chromatography over silica gel
  3. washto elute the product
  4. customcrystallized from 2-propanol
  5. customre-chromatographed
  6. customagain crystallized

Sources & evidence

ORD record
ord-39364203104b46139f0635d114ddab03
Source dataset
uspto-grants-1979_09
Patent number
US04167638

Linked notes

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